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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/38/1543883.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1543883
loop_
_publ_author_name
'Liu, Chengwei'
'Meng, Guangrong'
'Liu, Yongmei'
'Liu, Ruzhang'
'Lalancette, Roger'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 N-Acylsaccharins: Stable Electrophilic Amide-Based Acyl Transfer Reagents
 in Pd-Catalyzed Suzuki--Miyaura Coupling via N--C Cleavage
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b01836
_journal_year                    2016
_chemical_formula_sum            'C14 H9 N O4 S'
_chemical_formula_weight         287.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0936(6)
_cell_length_b                   10.3894(6)
_cell_length_c                   12.0481(7)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.67
_cell_volume                     1263.44(13)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11389
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.455
_diffrn_reflns_theta_min         5.623
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.545
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.218
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.060(5)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0293P)²+0.2990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2225
_reflns_number_total             2242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b01836_si_002.cif
_cod_data_source_block           151112RAL_YL_100K_0m_a
_cod_database_code               1543883
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.18781(5) 0.55476(4) 0.56422(4) 0.01172(14) Uani 1 1 d . .
O1 O -0.00163(15) 0.74411(15) 0.48805(13) 0.0204(3) Uani 1 1 d . .
O2 O 0.31876(15) 0.67603(14) 0.28879(12) 0.0181(3) Uani 1 1 d . .
O3 O 0.06941(14) 0.48089(13) 0.55433(13) 0.0170(3) Uani 1 1 d . .
O4 O 0.21185(14) 0.62443(14) 0.66417(12) 0.0164(3) Uani 1 1 d . .
N1 N 0.20183(17) 0.65959(15) 0.45462(14) 0.0129(4) Uani 1 1 d . .
C1 C 0.3018(2) 0.62362(19) 0.37612(17) 0.0140(4) Uani 1 1 d . .
C2 C 0.3724(2) 0.50986(19) 0.41974(18) 0.0135(4) Uani 1 1 d . .
C3 C 0.3251(2) 0.46505(19) 0.52003(16) 0.0136(4) Uani 1 1 d . .
C4 C 0.3794(2) 0.35905(19) 0.57369(19) 0.0166(4) Uani 1 1 d . .
H4 H 0.3455 0.3289 0.6425 0.020 Uiso 1 1 calc R U
C5 C 0.4854(2) 0.2996(2) 0.52185(19) 0.0204(5) Uani 1 1 d . .
H5 H 0.5265 0.2277 0.5565 0.025 Uiso 1 1 calc R U
C6 C 0.5331(2) 0.3428(2) 0.42029(19) 0.0201(5) Uani 1 1 d . .
H6 H 0.6052 0.2992 0.3864 0.024 Uiso 1 1 calc R U
C7 C 0.4774(2) 0.4482(2) 0.36758(18) 0.0172(4) Uani 1 1 d . .
H7 H 0.5100 0.4773 0.2980 0.021 Uiso 1 1 calc R U
C8 C 0.10281(19) 0.7554(2) 0.44013(18) 0.0144(4) Uani 1 1 d . .
C9 C 0.1359(2) 0.86614(19) 0.36697(18) 0.0139(4) Uani 1 1 d . .
C10 C 0.0474(2) 0.8978(2) 0.28290(18) 0.0162(4) Uani 1 1 d . .
H10 H -0.0309 0.8485 0.2723 0.019 Uiso 1 1 calc R U
C11 C 0.0746(2) 1.0020(2) 0.21473(19) 0.0199(5) Uani 1 1 d . .
H11 H 0.0174 1.0211 0.1543 0.024 Uiso 1 1 calc R U
C12 C 0.1850(2) 1.0784(2) 0.23414(18) 0.0202(5) Uani 1 1 d . .
H12 H 0.2021 1.1507 0.1881 0.024 Uiso 1 1 calc R U
C13 C 0.2704(2) 1.0490(2) 0.32107(18) 0.0188(5) Uani 1 1 d . .
H13 H 0.3439 1.1034 0.3363 0.023 Uiso 1 1 calc R U
C14 C 0.2486(2) 0.9404(2) 0.38571(18) 0.0172(4) Uani 1 1 d . .
H14 H 0.3099 0.9171 0.4421 0.021 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O4 119.12(9)
O3 S1 N1 110.26(9)
O4 S1 N1 108.26(8)
O3 S1 C3 110.55(9)
O4 S1 C3 113.08(9)
N1 S1 C3 92.21(9)
C8 N1 C1 126.65(17)
C8 N1 S1 118.72(13)
C1 N1 S1 113.59(13)
O2 C1 N1 124.23(19)
O2 C1 C2 127.43(19)
N1 C1 C2 108.28(17)
C3 C2 C7 120.30(19)
C3 C2 C1 114.48(19)
C7 C2 C1 125.2(2)
C2 C3 C4 122.55(19)
C2 C3 S1 111.11(15)
C4 C3 S1 126.29(16)
C5 C4 C3 116.7(2)
C5 C4 H4 121.7
C3 C4 H4 121.7
C4 C5 C6 121.4(2)
C4 C5 H5 119.3
C6 C5 H5 119.3
C7 C6 C5 121.3(2)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C2 117.8(2)
C6 C7 H7 121.1
C2 C7 H7 121.1
O1 C8 N1 119.15(19)
O1 C8 C9 123.68(19)
N1 C8 C9 117.17(16)
C10 C9 C14 120.81(19)
C10 C9 C8 118.05(18)
C14 C9 C8 121.05(18)
C11 C10 C9 119.2(2)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C12 120.4(2)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C13 120.0(2)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 120.1(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C9 119.3(2)
C13 C14 H14 120.4
C9 C14 H14 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4253(14)
S1 O4 1.4258(15)
S1 N1 1.7176(17)
S1 C3 1.753(2)
O1 C8 1.208(3)
O2 C1 1.197(3)
N1 C8 1.421(3)
N1 C1 1.432(3)
C1 C2 1.477(3)
C2 C3 1.380(3)
C2 C7 1.389(3)
C3 C4 1.390(3)
C4 C5 1.385(3)
C4 H4 0.9500
C5 C6 1.389(3)
C5 H5 0.9500
C6 C7 1.385(3)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.487(3)
C9 C10 1.390(3)
C9 C14 1.394(3)
C10 C11 1.386(3)
C10 H10 0.9500
C11 C12 1.388(3)
C11 H11 0.9500
C12 C13 1.391(3)
C12 H12 0.9500
C13 C14 1.388(3)
C13 H13 0.9500
C14 H14 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 569566
